The paper discusses the issue of race/ class hegemony which confronted the Black entrepreneurs in Barbados in the period 1900 to 1966. It examines how the Black entrepreneurs made their mark on the business landscape and provides a reinterpretation of earlier positions on the “rise” of Black entrepreneurs. It argues that the emergence of Black businesses was not simply a case of “rise”, but in several ways can be considered as resistance to the race/class hegemony of the planter-merchant class. That resistance, as in the case of the radical Workingmen’s Association of the 1920s, was illustrated by d explicit statements of intent to make inroads into sectors controlled by the upper classes. At times, as in the case of some enterprises, subtle statements or signs on the front of their businesses were indicative of the intent of the Black entrepreneurs. In other cases, it involved a rejection of the assumptions held by the elite class about the place of the black workers in the society. That rejection led to the encroachment of Black-owned businesses on sectors dominated by the planter-merchant class, without necessarily securing their displacement.